(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[2-[12-hydroxy-4,4,8,14-tetramethyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,2,3,5,6,7,9,10,11,12,13,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-6-methylhept-5-en-2-yl]oxyoxan-2-yl]methoxy]oxane-3,4,5-triol

Details

• Internal ID: 6ecfb8d5-5ac9-47bc-b7f4-5f1376b8a10c
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides
• IUPAC Name: (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[2-[12-hydroxy-4,4,8,14-tetramethyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,2,3,5,6,7,9,10,11,12,13,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-6-methylhept-5-en-2-yl]oxyoxan-2-yl]methoxy]oxane-3,4,5-triol
• SMILES (Canonical): CC(=CCCC(C)(C1CCC2(C1C(CC3C2(CCC4C3CCC(C4(C)C)OC5C(C(C(C(O5)CO)O)O)O)C)O)C)OC6C(C(C(C(O6)COC7C(C(C(C(O7)CO)O)O)O)O)O)O)C
• SMILES (Isomeric): CC(=CCCC(C)(C1CCC2(C1C(CC3C2(CCC4C3CCC(C4(C)C)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)C)O)C)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)O)O)O)C
• InChI: InChI=1S/C47H80O18/c1-21(2)9-8-14-47(7,65-43-40(59)37(56)34(53)29(63-43)20-60-41-38(57)35(54)32(51)27(18-48)61-41)24-13-16-46(6)31(24)26(50)17-25-22-10-11-30(44(3,4)23(22)12-15-45(25,46)5)64-42-39(58)36(55)33(52)28(19-49)62-42/h9,22-43,48-59H,8,10-20H2,1-7H3/t22?,23?,24?,25?,26?,27-,28-,29-,30?,31?,32-,33-,34-,35+,36+,37+,38-,39-,40-,41-,42+,43+,45?,46?,47?/m1/s1
• InChI Key: WHUNAZYGTKYZFF-BXLDJUIDSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₇H₈₀O₁₈
• Molecular Weight: 933.10 g/mol
• Exact Mass: 932.53446570 g/mol
• Topological Polar Surface Area (TPSA): 298.00 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): -0.42
• H-Bond Acceptor: 18
• H-Bond Donor: 12
• Rotatable Bonds: 13

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6877	68.77%
Caco-2	-	0.9010	90.10%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.7251	72.51%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8106	81.06%
OATP1B3 inhibitior	+	0.8189	81.89%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	+	0.6571	65.71%
P-glycoprotein inhibitior	+	0.7611	76.11%
P-glycoprotein substrate	-	0.6223	62.23%
CYP3A4 substrate	+	0.7223	72.23%
CYP2C9 substrate	-	0.8025	80.25%
CYP2D6 substrate	-	0.8264	82.64%
CYP3A4 inhibition	-	0.9502	95.02%
CYP2C9 inhibition	-	0.8671	86.71%
CYP2C19 inhibition	-	0.9036	90.36%
CYP2D6 inhibition	-	0.9380	93.80%
CYP1A2 inhibition	-	0.9057	90.57%
CYP2C8 inhibition	+	0.6809	68.09%
CYP inhibitory promiscuity	-	0.9413	94.13%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6474	64.74%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.9065	90.65%
Skin irritation	-	0.5956	59.56%
Skin corrosion	-	0.9488	94.88%
Ames mutagenesis	-	0.8100	81.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7928	79.28%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	+	0.5171	51.71%
skin sensitisation	-	0.8991	89.91%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	-	0.6032	60.32%
Acute Oral Toxicity (c)	I	0.5677	56.77%
Estrogen receptor binding	+	0.8066	80.66%
Androgen receptor binding	+	0.7617	76.17%
Thyroid receptor binding	-	0.5347	53.47%
Glucocorticoid receptor binding	+	0.6841	68.41%
Aromatase binding	+	0.6460	64.60%
PPAR gamma	+	0.7711	77.11%
Honey bee toxicity	-	0.5598	55.98%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9172	91.72%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	99.08%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.79%	91.11%
CHEMBL218	P21554	Cannabinoid CB1 receptor	96.03%	96.61%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.58%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.42%	96.09%
CHEMBL2996	Q05655	Protein kinase C delta	92.54%	97.79%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.80%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	91.29%	100.00%
CHEMBL226	P30542	Adenosine A1 receptor	91.21%	95.93%
CHEMBL259	P32245	Melanocortin receptor 4	90.24%	95.38%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.92%	94.45%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	87.54%	100.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.11%	85.14%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	86.71%	95.50%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	86.53%	97.14%
CHEMBL241	Q14432	Phosphodiesterase 3A	85.79%	92.94%
CHEMBL3714130	P46095	G-protein coupled receptor 6	84.32%	97.36%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.96%	95.89%
CHEMBL2581	P07339	Cathepsin D	83.68%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.99%	89.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	82.92%	93.04%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.81%	100.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.77%	92.62%
CHEMBL5028	O14672	ADAM10	80.56%	97.50%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.49%	95.83%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	80.36%	96.90%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	80.18%	100.00%

Plants that contains it

• Gynostemma pentaphyllum

Cross-Links

• PubChem: 5317917
• NPASS: NPC306656
• LOTUS: LTS0033515
• wikiData: Q105305842